Advice on Being a Boss

Getting to the C-suite isn't always as easy as it seems -- being a boss can be trying in new and challenging ways. Whether you need some help getting to be a boss, or now you're a boss and need advice on things like delegating and managing subordinates -- we've got you covered.

2016 Update: We still stand by these tips on delegating to your assistant — but you may also want to check out our latest discussion on how to delegate!

Reader E wonders what you can and should ask your assistant or secretary to do — and what is off limits. Great question!

I have been fortunate and I find myself a busy exec at a consulting firm at a young age. I am working 60-80 hours a week and just learning how to leverage my assistant. She is helping me with my expenses and time entry, but I suspect she and I could both get more out of the relationship. I’ve grown up in a world where I can do almost everything myself (like book travel) but I’m struggling to manage my work/life balance. I could use help with just about anything but as I dive into the world of asking for help, I don’t want to find myself at the other end of the spectrum where I’m asking too much or being inappropriate. Advice that outlines do and do not categories or mentions creative ideas might be most helpful.

Congrats to be a busy exec, and a special congrats on getting what sounds like a competent and helpful assistant — they can be hard to come by, so treat him or her like gold! (And apologies in advance for every time I say “her” meaning the assistant — in addition to being Reader E’s situation, it’s easier to type than “him or her” every time!) (Pictured: Screencap from Don’t Tell Mom the Babysitter’s Dead. We’re right on top of it, Rose!) Oh, and PSA: Don’t forget that tomorrow is Administrative Assistant’s Day. Check out our poll on what to get your assistant.)

Years ago, a friend explained to me that she always got her administrative assistant both flowers and cash: flowers so everyone in the office knows you appreciate your assistant, and cash to keep the assistant happy. My friend’s system made sense to me, so I never really looked for more than flowers — but I’m curious if other people get the assistant a personalized gift, or take him or her for lunch, or something else? Please comment in the thread about what you’re getting him or her — and how the equation changes if you share an assistant with other people.

Also, do you plan to celebrate Administrative Assistant’s Day or a full week? Just curious…

After last week’s how to dress like Linda Zwordling on Better Off Ted, we got a ton of comments about how beautifully dressed Portia de Rossi’s character, Veronica Palmer, is — and how much folks would love to chat with her stylist. We did some poking around and, lo and behold, found our way to Brandy Lusvardi, the costume designer for Better Off Ted. We just got off the phone with her, and thought we’d share our conversation…

2016 Update: We still stand by the advice in this post, but you may also want to check out our latest discussion of whether you can be friends with your secretary.

Can you be friends with your secretary? We got this e-mail from Reader A and it raises a lot of interesting questions, such as how to treat your assistants, how to behave in a male-dominated field where you’re one of the only women who isn’t a secretary, and so forth….

I’m wondering how one is friendly with colleagues at work without becoming friends with colleagues at work. I’m an attorney and have recently moved to a firm where I’m the only female attorney, and the staff is comprised almost entirely of women. I was warned in a joking manner by one of the partners when taking the job to beware – previous female attorneys at the firm have fallen victim to being ‘friends’ with staff (regular lunches, after-work drinks, etc) and then later suffer the wrath should someone need to be called on the carpet for job performance or with claims of favoritism.

So far, I’ve gone to lunch with only a couple of people who have initiated the invitation, and I avoid discussing others in the office and steer conversation away from that topic. However, I plan on being here a long time, and I wonder if you or your readers have insight that might help me or have found themselves in similar situations.

Right? Great e-mail. So far, what reader A is doing sounds great to us. Here are some further tips:

There’s nothing wrong with finding a friend who happens to be a staffer. Like our advice for dating at the office a few weeks ago, though, we would not recommend looking for a best friend at the office (really, among the staffers or elsewhere). Aim for collegiality. You’re all in this together, and you all have your own jobs to do, and it’s often best if emotions are kept out of it. Friendship can be harder with people you supervise directly — it’s important to see both their skills and weaknesses as clearly as possible, so you can compensate and better manage, either by delegating things in certain respects, or knowing to phrase your requests in a certain way.

A number of readers have written in asking about holiday presents for administrative assistants. We tend to agree with Above the Law’s advice last year — cash is the way to go for holidays. Still, we thought we’d poll people to see what they’re giving (and how much):